1. Field of Invention
The present invention relates to novel acetic acid derivatives of 3-aryl-2,1-benzisoxazole, including esters, amides, and metal salts thereof, methods of preparation, pharmaceutical methods and compositions for treating living animals for inflammation therewith, and the novel acetonitrile intermediates for the preparation thereof.
2. Description of the Prior Art
Preparation of the 3-aryl-2,1-benzisoxazoleacetic acids and derivatives of the present invention has not previously been reported in the literature. A failed attempt to make a compound having the structure falling within the scope of the present invention, namely the compound structure: ##STR2## was reported in J. HETEROCYCLIC CHEM. 14, 1225 (1977).
Aryl benzoxazoleacetic acids having the formula: ##STR3## have been reported in J. MED. CHEM. 18, 53 (1975); 20 169 (1977) and 20, 797 (1977). In these references the oxygen and nitrogen are separated by the carbon bearing the aryl group whereas they are adjacent in the present invention.
Aryl-1,2-benzisoxazoleacetic acids having the formula: ##STR4## have been reported in J. MED. CHEM. 22, 1554 (1979).
In this reference the oxygen is adjacent to the phenyl moiety of benzoxazole ring, whereas in the present invention the nitrogen is adjacent.
Conversion of 2-aminobenzophenones to 3-aryl-2,1-benzisoxazoles; i.e., 3-arylanthranils, has long been known, C.A. 62, 16,157 (1965).
5-Carboxy-3-phenyl-2,1-benzisoxazole and its methyl ester are known, C.A. 77, 164,573e as is 6-carboxy-3-phenyl-2,1-benzisoxazole, C.A. 90, 186,909q.
2-Phenyl-6-benzoxazoleacetonitrile and its .alpha.-methyl derivative are known, C.A. 87, 62,486t. 2-Phenyl-5-benzoxazoleacetonitrile and its .alpha.-methyl derivative are known, C.A. 80, P70,798a; C.A. 81, P105,488r; C.A. 82, 118,774b and C.A. 85, P142,806w. These compounds are isomers only and not useful intermediates in preparation of compounds of Formula I.